This invention relates to N-(heterocyclicaminocarbonyl)arylsulfonamide agricultural chemicals.
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR1## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al. Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR2## wherein R is butyl, phenyl or ##STR3## and R.sub.1 is hydrogen or methyl. When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR4## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (i), and their use as general or selective herbicides, ##STR5## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 W is oxygen or sulfur; PA1 X is --NHCH.sub.3 or --N(CH.sub.3).sub.2 ; PA1 Z is methyl or methoxy; and PA1 A is ##STR8## or N and their agriculturally suitable salts provided that when R.sub.2 is nitro or trifluoromethyl, R.sub.3 can not be nitro or trifluoromethyl. PA1 W is oxygen PA1 1. 2-chloro-N-[(4-methoxy-6-methylamino-1,3,5-triazin-2-yl)aminocarbonyl]benz enesulfonamide, m.p. 224.degree.-228.degree. C.; PA1 2. 2-chloro-N-[(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)aminocarconyl]be nzenesulfonamide, m.p. 200.degree.-206.degree. C.; PA1 3. N-[(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-methylbe nzenesulfonamide, m.p. 194.degree.-198.degree. C.; PA1 4. N-[(4-methoxy-6-methylamino-1,3,5-triazin-2-yl)aminocarbonyl]-2-methylbenz enesulfonamide, m.p. 199.degree.-202.degree. C.; and PA1 5. N-[(4-dimethylamino-6-methoxypyrimidin-2-yl)aminocarbonyl]-2-methylbenzene sulfonamide, m.p. 238.degree.-239.degree. C. PA1 6. N-[(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-nitroben zenesulfonamide, m.p. 212.degree.-213.degree. C. PA1 7. N-[(4-methylamino-6-methoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-nitrobenze nesulfonamide.
Compounds of Formula (ii), and their use as antidiabetic agents, are reported in J. Drug Res. 6, 123 (1974). ##STR6## wherein R is pyridyl.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, wheat, and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving the efficiency.
A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, however, for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops.